ω-Aryl-inter-oxa-9-deoxy-PGD1 compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.

The present application is a divisional application of Ser. No. 809,249,filed June 23, 1977, now U.S. Pat. No. 4,142,052 issued Feb. 27, 1979;which is a divisional application of Ser. No. 614,244, filed Sept. 17,1975, now pending. Likewise, U.S. Ser. No. 809,248, filed June 23, 1977,now U.S. Pat. No. 4,099,014 issued on July 4, 1978, is a divisionalapplication of Ser. No. 614,244.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,099,014.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein Y iscis-CH═CH--, trans-CH═CH--, or --CH₂ CH₂ --;wherein Z₅ is (1) --CH₂--O--CH₂ --(CH₂)_(g) --CH₂ --, (2) --(ch₂)₂ --o--(ch₂)_(g) --CH₂ --, or(3) --(CH₂)₃ --O--(CH₂)_(g) --,Wherein g is one, 2, or 3; Wherein M₁ is##STR3## wherein R₅ and R₆ are hydrogen or methyl, with the proviso thatone of R₅ and R₆ is methyl only when the other is hydrogen; Wherein L₁is ##STR4## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being thesame or different, with the proviso that one of R₃ and R₄ is hydrogen orfluoro only when the other is hydrogen or fluoro; Wherein Z₃ is oxa ormethylene;Wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms,inclusive, and s is zero, one, 2, or 3, the various T's being the sameor different, with the proviso that not more than two T's are other thanalkyl, with the further proviso that Z₃ is oxa only when R₃ and R₄ arehydrogen or methyl, being the same or different; andwherein R₁ ishydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to10 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms,inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenylsubstituted with one, two, or three chloro or alkyl of one to 3 carbonatoms, inclusive, or a pharmacologically acceptable cation; with thefurther proviso that D is ##STR5## only when Y is --CH₂ CH₂ --.
 2. Acompound according to claim 1, wherein M₁ is ##STR6##
 3. A compoundaccording to claim 1, wherein M₁ is ##STR7##
 4. A compound according toclaim 3, wherein D is ##STR8## and Y is --CH₂ CH₂ --.
 5. A compoundaccording to claim 4, wherein Z₃ is methylene.
 6. A compound accordingto claim 5, wherein s is zero or one and T is chloro, fluoro, ortrifluoromethyl.
 7. A compound according to claim 6, wherein g is one.8. A compound according to claim 7, wherein R₅ and R₆ are both hydrogen.9. A compound according to claim 8, wherein R₃ and R₄ are both hydrogen.10.5-Oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-9,10-didehydro-9-deoxy-PGD₁,a compound according to claim
 9. 11. A compound according to claim 4,wherein Z₃ is oxa.
 12. A compound according to claim 11, wherein s iszero or one and T is chloro, fluoro, or trifluoromethyl.
 13. A compoundaccording to claim 3, wherein D is ##STR9##
 14. A compound according toclaim 13, wherein Z₃ is methylene.
 15. A compound according to claim 14,wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.16. A compound according to claim 15, wherein g is one.
 17. A compoundaccording to claim 16, wherein R₅ and R₆ are both hydrogen.
 18. Acompound according to claim 17, wherein R₃ and R₄ are both hydrogen. 19.5-Oxa-17-phenyl-18,19,20-trinor-9-deoxy-PGD₁, a compound according toclaim
 18. 20. A compound according to claim 13, wherein Z₃ is oxa.
 21. Acompound according to claim 20, wherein s is zero or one and T ischloro, fluoro, or trifluoromethyl.
 22. A compound according to claim21, wherein g is one.
 23. A compound according to claim 22, wherein R₅and R₆ are both hydrogen.
 24. A compound according to claim 23, whereinR₃ and R₄ are both hydrogen. 25.5-Oxa-16-phenoxy-17,18,19,20-tetranor-9-deoxy-PGD₁, a compound accordingto claim 24.